Winter Timeshare Rentals
Winter getaways are always popular, making now the perfect time to secure exclusive timeshare deals for your seasonal escape! Whether you're dreaming of a snowy mountain retreat or a warm-weather getaway, these timeshare rentals offer the perfect setting to make your winter vacation unforgettable.
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 23–28, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,186 ($637/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 23–29, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,150 ($358/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,831 ($404/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 23–28, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,179 ($436/night)
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WorldMark Scottsdale
Scottsdale, Arizona- Jan 23 – Feb 20, 2027 (28 nights)
- 1 bed/1 bath, sleeps 4
- $5,849 ($209/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,977 ($711/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 23–30, 2027 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $10,380 ($1,483/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,431 ($490/night)
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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $12,015 ($1,716/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
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The Ritz-Carlton Club, Aspen Highlands
Aspen, Colorado- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $12,996 ($1,857/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,701 ($957/night)
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Voted Top Pick 2026
Marriott's Desert Springs Villas II
Palm Desert, California- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,492 ($1,070/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,786 ($827/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,832 ($547/night)
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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Jan 23–30, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,731 ($533/night)
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The Westin Riverfront Mountain Villas
Avon, Colorado- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,801 ($829/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,328 ($1,047/night)
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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,740 ($820/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($315/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Grand Lodge on Peak 7
Breckenridge, Colorado- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $6,292 ($899/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Jan 23 – Feb 2, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($678/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,151 ($1,164/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 23–26, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($240/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 23–26, 2027 (3 nights)
- 3 bed/2 bath, sleeps 8
- $901 ($300/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,510 ($930/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)